The best things to do in Chicago this week

Get ready, punk rockers! Riot Fest is returning to Douglass Park from September 18-20 with a laundry list of rock, punk, metal and emo artists. It's always one of the biggest music fests of the season thanks to a must-see lineup of both legacy acts and emerging newcomers. 

750 swimmers will be making waves in the Chicago River Swim, benefitting ALS research at Northwestern University, youth swim education in underserved communities and programs aimed at closing the racial gap in swim access. Swimmers will launch near the Dearborn Street Bridge and finish at the Clark Street Bridge. Spectators can line the Chicago Riverwalk to cheer them on as participants tackle 1- and 2-mile courses.

A celebration of storytelling across mediums comes to life on stage with "live journalism show" Chicago Story Fest at Athenaeum Center in Lakeview. Journalists, comedians, dancers, singers, filmmakers and musicians from Chicago will share their personal stories centered around this year's theme, "Villains: Stories about what we fear, what we misunderstand, and what we become."

Navy Pier’s annual performing arts festival welcomes more than 100 local artists for a weekend of music and performances spread across five stages. Featured acts range from Chicago’s world-class stalwarts to many exciting up-and-comers. 

More than 70 institutions, galleries and programming partners are coming together this fall for the fourth annual Chicago Exhibition Week. The 7-day event is a celebration of the city's diverse art scene, featuring a lineup of talks, networking events, workshops, performances, activations, parties and more, many of which are free to attend.

Send summer off with a bang at this indoor/outdoor music and arts festival in suburban Bridgeview (7337 W 100th Pl, Bridgeview, IL, 60456), which has been held on the last Saturday of the summer since its debut in 2024. This year, EDM duo Big Gigantic headlines, alongside Saxsquatch, Henry Fong, The Sponges and more. Check out the full lineup here.

For this year's edition of Eataly's annual fall fest, the marketplace is transforming its store into an Italian Piazza with 15 drink stations and more than 30 food stations for an all-you-can-eat evening. As always, the fest will also include live music, indoor lawn games, raffles and take-home goodies. Mangia!

Antique vendors and classic cars fill six blocks of Roscoe Village at this three-day throwback street fest, where everything old is new again. The music lineup is usually equally nostalgic, featuring tribute acts that perform hits from the ‘80s and ‘90s. 

The Lincoln Park Chamber of Commerce hosts the neighborhood's Uncorked Wine Stroll, an evening showcasing Lincoln Park businesses with plenty of vino along the way. With over a dozen stops along Lincoln Avenue, light bites, free pedicab rides and—of course—lots of wine, there’s no better way to get to know the neighborhood. Cobble together a group of five or more to save $5 per ticket.

Savor the season with a sip-and-shop wine stroll down Division Street. The route takes you to six participating locations, including Lost Girls Vintage and Makoma House, where you'll be able to fill up on vino along the way. A ticket gets you 12 2-ounce pours and light bites, plus a commemorative tasting glass.

The celebration at the DANK Haus German American Cultural Center in Lincoln Square might be the closest you'll get to the actual Oktoberfest without hopping on a plane. The festive evening will have authentic German food and beer, live music, games, a stein-holding competition, a ceremonial keg tapping and even a yodeling contest. Ticket sales support the non-profit organization's mission to preserve German culture, language and traditions in Chicago.

Guinness Open Gate Brewery is hosting a spirited three-day Oktoberfest bash in the West Loop. Expect live polka, oompah and contemporary music, stein-holding contests and Bavarian fare like schnitzel, giant pretzels and sausages. Plus, you can take home your commemorative beer stein for a small fee.

Celebrate Oktoberfest over the course of three weekends at The Northman Beer & Cider Garden, which is bringing a host of festivities to its Riverwalk digs this September and early October. Expect giant pretzels and German sausages, beer steins and polka music, and scenic waterfront views with a European vibe.

Chicago's largest Oktoberfest celebration is returning to the heart of Fulton Market. Located just behind Restaurant Row at 171 N. Peoria St., this lively six-week German fest is pouring Hofbräu München beer imported directly from Germany. Guests can also expect Bavarian pretzels, brats, live German music, carnival games and more. 

Explore Chicago's eerie past as you snake down the river aboard the First Lady Creepy Cruise. The 90-minute tour combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.

The oldest music festival in North America plays host to more than 90 shows throughout summer, featuring big-name headliners like Paul Simon, Alabama Shakes and Chance the Rapper. Check out the full schedule of artists coming to Highland Park this year, and don't forget to pack a picnic.

Brookfield Zoo's Carousel Plaza is transforming into a German-inspired celebration feature family-friendly fun with polka music, dancing, games, giveaways and more. The Oktoberfest event is included with admission and will offer a special seasonal menu with bratwurst, specialty beers, pretzels with cheese and more available for purchase.

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running for 30 minutes on Thursdays through Saturdays, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Get your heart rate up in a mat Pilates class on The St. Regis Chicago's luxe rooftop Terrace. After class, which includes a fitness mat that's yours to take home, guests can enjoy the sprawling 12,000-square-foot wellness floor, complete with an indoor pool, sundeck, sauna, steam room, fitness studios are more.

Sportsman's Club's Sunday BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This year's lineup includes Bar Bambi, Pizz'amici, Milli by Metric, Kimski, Mister Tiger, Diego and more.

Explore notable Impressionist Mary Cassatt's works in the first exhibit in more than 25 years dedicated solely to the American artist at the Art Institute. Known for her works depicting mothers with children and intimate caretaking scenes, Cassatt was the only American to join the French Impressionists. After Impressionism showcases paintings, pastels and prints from the time in her career when she began to take her art in a new direction.

Whether it's on a minibus or on foot, this tour takes you to the locations frequented by some of Chicago's most notorious gangsters and the places that have been haunted by their ghosts. With four tours offered daily, there's always an opportunity to take a step back in time to learn about figures like Al Capone and Chicago's haunted history.

Grab your dirndls and lederhosens and get ready to party at the second annual Old Town Oktoberfest. The three-day German-inspired fest will have brats, pretzels and German beer, plus live entertainment all weekend. Guests can also participate in stein-holding contests, and dance and sing the night away.

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting.

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

“Willem de Kooning Drawing” is the first exhibition to explore the full scope of the artist's drawing practice, framing it as the foundation of his boundary-breaking career. Featuring more than 200 artworks—including rarely seen drawings alongside paintings, sculptures and prints—this exhibition offers an unprecedented opportunity to experience seven decades of his graphic production while shedding light on his constant experimentation with various materials, tools and techniques.

The newly opened Obama Presidential Center is celebrating the country's 250th anniversary with its inaugural "You Are America" series this summer. The series kicks off on July 4 with The People's Fourth, a free event featuring live music, self-guided tours and other family-friendly activations across the campus. Other series highlights include House Music on the Plaza, Garden Gatherings and an Art in Action talk with Obama Presidential Center-commissioned artist Mark Bradford. Check out the full schedule of You Are America events here.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

This first-of-its-kind exhibition at the Museum of Contemporary Art Chicago explores the visual, political and spiritual histories of dancehall and reggaetón through contemporary art. Once grassroots scenes, both genres have become globally influential movements tied closely to sexual and political liberation. The show features works by more than 35 artists, including Jean-Michel Basquiat, Edra Soto, supakid and Lee “Scratch” Perry.

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Foundation Center River Cruise takes place aboard a Chicago’s First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline. 

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding. Admission is free on Friday, June 12 in honor of what would have been Anne's 97th birthday. Guests can also enjoy the exhibit for free with the purchase of a general admission ticket for the rest of the weekend.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrive properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. Every corner is crafted to ignite curiosity and inspire a sense of awe, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, Drunk Dracula, on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

Every Wednesday, the Old Town School of Folk Music hosts a showcase of world music and dance. Featuring both local and touring talent, you're sure to hear something new and exciting at this long-running series. Before the show, be sure to peruse the Old Town School of Folk Music Store, where you can rent instruments, learn about lessons and peruse a wide selection of books.